There is a difference in acidity of the hydrogens labeled red below. Select all the distinguishing factors (ARIO concept) that make one compound more acidic than the other. Do not select aspects of the ARIO concept that apply to both compounds equally. H. H pKa = 31 pKa = 41 Select one or more: the ARIO concept does not apply to this example O the negative charge is stabilized in the more acidic compound by occupying a hybrid orbital of higher s character O the negative charge in the more acidic compound can be stabilized on a more electronegative atom (when comparing all resonance structures) O the negative charge is better resonance stabilized in the more acidic compound by having more resonance structures O the negative charge in the more acidic compound is stabilized by a stronger inductive effect

There is a difference in acidity of the hydrogens labeled red below. Select all the distinguishing factors (ARIO concept) that make one compound more acidic than the other. Do not select aspects of the ARIO concept that apply to both compounds equally. H. H pKa = 31 pKa = 41 Select one or more: the ARIO concept does not apply to this example O the negative charge is stabilized in the more acidic compound by occupying a hybrid orbital of higher s character O the negative charge in the more acidic compound can be stabilized on a more electronegative atom (when comparing all resonance structures) O the negative charge is better resonance stabilized in the more acidic compound by having more resonance structures O the negative charge in the more acidic compound is stabilized by a stronger inductive effect

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.48AP: As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more...

See similar textbooks

Similar questions

Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)
As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone.
Histamine, whose release in the body triggers nasal secretions and constricted airways, has three nitrogen atoms. List them in order of increasing basicity and explain your ordering.
Arrange the compounds in each set in order of increasing base strength. consult Table 4.1 for pKa values of the conjugate acid of each base.
Place the following compounds in order of relative acidity. Consider 1 to be the most acidic and 6 to be the least acidic.
Rank the following compounds in terms of increasing acidity (least acidic first). Explain your ranking. Making sure to say which hydrogen in each molecule is the most acidic, and discuss the relative stability of the conjugate bases.
What is the correct way to arrange the numbered protons in increasing order of acidity and why?
rank the following species in order of increasing acidity. least acidic should be on top. CBrH2COOH CBr2HCOOH CH3COOH CBr3COOH
Among the sets of acids, which is/are correctly arranged according to INCREASING acidity? One or more sets may be chosen. Explain why. a. HBr < H2Se < AsH3 b. CH4 < PH3 < H2S c. H2S < H2Te < H2Se d. HSO3– < H2SO3 < H2SO4
In the group of mixture of Trans-cinnamic acid, isovanillin and stilbene, which compound is most acidic and which one is the least acidic. determine acidity based on molecular structure
Which of the following correctly places the three compounds in order of increasing acidity? H3BO3 < HClO3 < H2SO3 H2SO3 < H3BO3 < HClO3 HClO3 < H2SO3 < H3BO3 H3BO3 < H2SO3 < HClO3
Rank the following acids in order from weakest acid to strongest acid. Explain why you ranked the acids in the designated order. Your answer should include, if applicable, reasons based in inductive effects, resonance (electron donating groups vs electron withdrawing groups), etc.